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Hard surface cleaners based on compositions derived from natural oil metathesis

a technology of compositions and hard surfaces, applied in the field of hard surface cleaners, can solve the problems of difficult production and general poor satisfactory material quality

Active Publication Date: 2013-08-29
STEPAN COMPANY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The patent text claims that the aqueous cleaners tested in the text are able to perform just as well or better than commercial cleaners in a standard test.

Problems solved by technology

These materials are generally less than completely satisfactory, however, because compounds having such large carbon chains can behave functionally as soil under some cleaning conditions.
Cross-metathesis of unsaturated fatty esters with olefins generates new olefins and new unsaturated esters that can have reduced chain length and that may be difficult to make otherwise.

Method used

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  • Hard surface cleaners based on compositions derived from natural oil metathesis
  • Hard surface cleaners based on compositions derived from natural oil metathesis
  • Hard surface cleaners based on compositions derived from natural oil metathesis

Examples

Experimental program
Comparison scheme
Effect test

example 1a

Cross-Metathesis of Soybean Oil and 1-Butene

[0082]A clean, dry, stainless-steel jacketed 5-gallon Parr reactor equipped with a dip tube, overhead stirrer, internal cooling / heating coils, temperature probe, sampling valve, and relief valve is purged with argon to 15 psig. Soybean oil (SBO, 2.5 kg, 2.9 mol, Costco, Mn=864.4 g / mol, 85 weight % unsaturation, sparged with argon in a 5-gal container for 1 h) is added to the Parr reactor. The reactor is sealed, and the SBO is purged with argon for 2 h while cooling to 10° C. After 2 h, the reactor is vented to 10 psig. The dip tube valve is connected to a 1-butene cylinder (Airgas, CP grade, 33 psig headspace pressure, >99 wt. %) and re-pressurized to 15 psig with 1-butene. The reactor is again vented to 10 psig to remove residual argon. The SBO is stirred at 350 rpm and 9-15° C. under 18-28 psig 1-butene until 3 mol 1-butene per SBO olefin bond are transferred into the reactor (˜2.2 kg 1-butene over 4-5 h).

[0083]A toluene solution of [1,3...

example 1b

[0086]The procedure of Example 1A is generally followed with 1.73 kg SBO and 3 mol 1-butene / SBO double bond. An aliquot of the product mixture is transesterified with sodium methoxide in methanol as described above. The products (by GC) are: methyl 9-decenoate (24 wt. %), methyl 9-dodecenoate (18 wt. %), dimethyl 9-octadecenedioate (2 wt. %), and methyl 9-octadecenoate (2 wt. %).

example 1c

[0087]The procedure of Example 1A is generally followed with 1.75 kg SBO and 3 mol 1-butene / SBO double bond. An aliquot of the product mixture is transesterified with sodium methoxide in methanol as described above. The products (by GC) are: methyl 9-decenoate (24 wt. %), methyl 9-dodecenoate (17 wt. %), dimethyl 9-octadecenedioate (3 wt. %), and methyl 9-octadecenoate (2 wt. %).

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Abstract

Aqueous hard surface cleaner compositions derived from metathesized natural oil feedstocks are disclosed. In one aspect, the compositions comprise at least one anionic surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, 5 octadecene-1,18-dioic acid, or their ester derivatives. In another aspect, aqueous hard surface cleaners comprising at least one nonionic or amphoteric surfactant derived from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. The aqueous cleaners noted above rival or outperform commercial baselines in a Gardner straight-line washability test. Industrial degreasers comprising a C10 or C12 amide solvent and derived from a metathesis-derived C10-C17 monounsaturated acid are superior to commercial standards.

Description

FIELD OF THE INVENTION[0001]The invention relates to hard surface cleaners, and particularly to compositions useful therein as surfactants or solvents that derive from natural oil metathesis.BACKGROUND OF THE INVENTION[0002]Hard surface cleaners continuously evolve and adapt to customer demands, changing times, and increasingly strict health and environmental regulations. Successful hard surface cleaners can remove greasy dirt from smooth or highly polished surfaces and disinfect them without leaving behind noticeable films or streaks. Modern aqueous cleaners, designed primarily for home or institutional use, typically include one or more surfactants in addition to water. Commonly, the cleaners include a small proportion of low-toxicity organic solvent(s), antimicrobial agents, buffers, sequestering agents, builders, bleaching agents, hydrotropes, and other components. As formulators seek to create more environmentally friendly products, they often reduce the amount of solvent(s), b...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C11D1/28C11D1/83C11D1/94C11D1/92C11D1/04C09K23/00C09K23/08
CPCC07C69/533C07C69/593C11D1/28C11D1/74B01F17/0028B01F17/0057C07C209/12C07C231/12C07C303/18A01N25/30C07C211/21C07C237/16C11D1/90C11D1/92C09K15/28C09K8/00A62D1/0071A61Q19/10A61Q5/12A61K8/466A61K8/44A61K8/42A61K8/416A01N41/04A01N37/44A01N37/18A01N25/04C11D1/62C11D1/04A61K8/92A01N25/02C11C3/00C08K5/20C08K5/01C11D3/48C07C219/08A01N33/12C11D1/83C11D1/94C11D1/002C11D1/652C08G65/2615C11C3/08C07C211/63C07C211/64C07C233/38C07C309/14A01N33/18A01N39/04A01N43/653A01N51/00A01N57/20A01N43/40A01N43/56A01N53/00C09K23/00C07C6/04C07C41/03C07C43/11C07C67/26
Inventor ALLEN, DAVE RBERNHARDT, RANDAL JBROWN, AARONMASTERS, RONALD A.WOLFE, PATRICK SHANETITIEVSKY, LENA
Owner STEPAN COMPANY
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